We stayed at the Essex House last year. Concierge was helpful and guided us to what, for us, was the perfect experience.

Our requirements: Avoid too much security, not stand out in the cold for hours, and willing to spend some $$ for the above.

http://redeyegrill.com/home

The Redeye Grill had a late seating 5 course dinner menu which allowed for a long, pleasant dinner, and then they had their patio and sidewalk in front of the restaurant blocked off so we could step out at midnight to watch the ball drop.

We had a clear, albeit not up close, live view of the ball dropping.

And stayed warm, had a much (much!) better than expected dinner and drinks, and were able to get to the restaurant and back to our hotel without too much difficulty.

All for about $250 per person, which may not be attractive for those of you with kids...